Washington — Republican Jeb Bush announces his candidacy for president Monday, and he will highlight his record as a two-term governor of Florida, 1999 to 2007 – a record that is plenty conservative, his supporters say.

From taxes and privatization to education and affirmative action, Mr. Bush moved Florida to the right. And on the biggest controversy of his tenure, the case of a brain-damaged woman on life support, Bush took the social conservative position and intervened to keep her alive.

But that was then. Now, in 2015, he is struggling to convince conservatives that he’s one of them. And he won’t budge on the two issues of the day that are holding him back: his support for legal status for undocumented immigrants, and his support for the state-driven education standards known as Common Core.

“In Florida, he’s still perceived as conservative, especially on fiscal issues and even on social issues,” says Susan MacManus, a political scientist at the University of South Florida in Tampa. “But the immigration issue has gotten such play, and he’s been so strong on that issue, as he has, increasingly, on education.”

The question is whether Bush can communicate the entirety of his record, and then show GOP primary voters how his views on immigration and education fit into a larger, conservative vision for the country. At a GOP economic forum hosted by Florida Gov. Rick Scott (R) on June 2, Bush conveyed a sense of urgency about immigration.

“We need immigration reform, for crying out loud,” Bush said. “A broken immigration system is a drain on our economy.”

He also pitched education standards as a way to make Americans economically competitive. But he avoided the words “Common Core,” which makes the concept more palatable, says Ms. MacManus.

Bush has lined up prominent Florida conservatives to endorse his candidacy, including state Attorney General Pam Bondi and Rep. Daniel Webster. But the key to breaking out of the large Republican presidential field and seizing the nomination could be his ability to explain his record as governor.

Bush cut taxes. During eight years as governor, Bush-backed legislation cut taxes by $19 billion. The biggest cut came from the reduction and then elimination of the Intangible Personal Property Tax – taxes levied on stocks, bonds, mutual funds, money market funds, and similar investments.

Job growth was robust. Under Bush, a net 1.3 million were created in Florida, more than in Texas during that same period. Politifact Florida verified those numbers, but added that “it’s worth noting that no governor is solely, or even mostly, responsible for economic growth in their state.”

Bush was big on privatization. He reduced the government workforce by 13,000, or 11 percent, during his tenure. Politifact Florida verified that number, but adds that privatizing state jobs “doesn’t mean it’s necessarily cheaper or better for taxpayers.”

Bush was an education governor. He introduced a statewide school voucher plan, the first in the nation. It provided tax-paid vouchers for students in low-performing public schools to attend private school. Bush also expanded charter schools, put in place test-based accountability for students and schools, and instituted a letter-grade rating system for schools.

Bush tackled affirmative action. In 1999, his “One Florida” initiative eliminated affirmative action in admissions to state universities and in some state contracts – the first change in how the state sought to promote diversity in decades. The program sparked protests and alienated African-American voters. Bush says that One Florida led to more black and Hispanic students in the state university system. Politifact Florida confirms that is true, but notes that the percentage of minorities in the system is down.

Bush played major role in Terri Schiavo case. As a practicing Roman Catholic, Bush describes himself as a “pro-life person.” In 2003, he acted on that belief in the case of Ms. Schiavo, a Florida woman who had been on life support since 1990. The Florida legislature granted Bush the authority to intervene in the case, but the law was found unconstitutional.

The Schiavo case could be tricky for Bush’s campaign. He can use it to woo social conservatives, but general election voters may not be as sympathetic. Public opinion at the time did not support Bush’s position.